Alvin Bailey, New York City

What We Like: Remember when every men's publication praised the double-breasted suit? We do, because we did. Well, just because it's not making headlines these days doesn't mean it's not relevant. It's a classic, like Alvin proves here. He's also added the right accessories: patterned tie, pocket square, a larger watch (which matches his stature), sunglasses, and a badass car. Props.